Sodium Hydroxide → Methyl hydrogen 2-nitroterephthalate

HRID 365646Notes

Reaction equation

HRID 365646 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])([O-:5])=[O:4]>O1CCOCC1.O>[C:16]([C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:3]([O-:5])=[O:4])[CH:15]=1)([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21364Dimethyl nitroterephthalate

Product 1

HCID 98592Methyl hydrogen 2-nitroterephthalateYield 71,684%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1N NaOH (50 mL) was slowly added dropwise at room temperature over 30 min to a stirred solution of di-methyl nitroterephthalate (12 g, 0.05 mmol) in dioxane (100 mL). After stirring overnight at room temperature the reaction was diluted with water, washed with ether, acidified with 1N HCl (50 mL) and extracted with ethyl acetate. After drying the ethyl acetate phase (MgSO4) and evaporation, the resulting residue was purified by flash chromatography (silica gel, 98:2:0.1 CHCl3 :MeOH:HOAc) to yield the title compound (8.07 g, 72%).

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. customthe ethyl acetate phase (MgSO4) and evaporation
  5. customthe resulting residue was purified by flash chromatography (silica gel, 98:2:0.1 CHCl3 :MeOH:HOAc)

Sources & evidence

ORD record
ord-f0cd059d27b14ac48dc29904efeefe8f
Source dataset
uspto-grants-2000_10
Patent number
US06127359

Reaction notes

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